<i>N</i>-Oxidation of primary and secondary amines to give hydroxylamines—a general metabolic route

Beckett, A. H.; al-Sarraj, S

doi:10.1111/j.2042-7158.1972.tb08918.x

Cited by 35 publications

(8 citation statements)

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“…Qualitative identification of arylhydroxylamines by thin-layer chromatography with the use of various spray reagents has also been described (4). In addition, some gas chromatographic determinations of arylhydroxylamines have been reported (5,6).…”

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Colorimetric determination of N-arylhydroxylamines with 9-chloroacridine

Gammans¹,

Stewart²,

Sternson³

1974

Anal. Chem.

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sis. SRM paint was analyzed by polarography and atomic absorption. The reasonably good agreement between 252Cf activation analysis and the other methods demonstrates the reliability and utility of the isotope source technique for this determination.Irradiation for 2 hours with the 600-Mg 252Cf source followed by 100 minutes of counting with a 60-cm3 Ge(Li) detector yields about 7 counts of the 204>«Pb isotope per milligram of lead. For a paint sample weighing 1.5 grams, the lower limit of determination would be of the order of 1%.As noted, analysis of the Ge(Li) spectrum of those elements likely to be major or minor constituents of paint indicates that they will not interfere in the quantitation of the gamma ray lines of 204mPb. Self-shielding effects due to the matrix are expected to be negligible since the nuclear reaction involves fast neutrons and a paint sample is unlikely to contain appreciable amounts of neutron moderating elements.The results presented here indicate that with a 252Cf source of several tens of milligrams and the 60-cm3 Ge(Li) detector, the determination of •~1% of lead in a sample of 1-2 grams of paint could be accomplished with a 15-minute irradiation and 15-minute counting. The potential exists for largely automating the irradiation and counting of a large number of samples. Hence, it would appear possible that although the initial cost of equipment for this determination would be greater than for alternate methods, the speed and adequate reliability of the isotope source method would make it economically competitive.

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confidence: 99%

Colorimetric determination of N-arylhydroxylamines with 9-chloroacridine

Gammans¹,

Stewart²,

Sternson³

1974

Anal. Chem.

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“…The hydroxylamine intermediate, formed by oxidation of the secondary amine, if present, is rarely observed in vivo for piperazines or other nitrogen-containing alicycles. An explanation for this may be found in reports that this intermediate is inherently unstable (Beckett and Salami, 1972;Beckett et al, 1977;Franklin et al, 1977;Ziegler, 1987); however, identifications of stable alicyclic hydroxylamines have been made (Beckett and al-Sarraj, 1972;Achari and Beckett, 1983;Rodriguez and Acosta, 1997;Zhang et al, 2000). There are even fewer examples of glucuronic acid conjugation of alicyclic hydroxylamines in the literature (Straub et al, 1988;Delbressine et al, 1992;Schaber et al, 2001), and the structures of these metabolites have been largely deduced from mass spectrometry and in some cases 1 H NMR analysis.…”

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confidence: 99%

Identification of a Hydroxylamine Glucuronide Metabolite of an Oral Hypoglycemic Agent

Miller¹,

Doss²,

Stearns³

2004

Drug Metab Dispos

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This article is available online at http://dmd.aspetjournals.org ABSTRACT:Glucuronides of piperazine hydroxylamines are rarely reported in the literature, and even more rarely are their structures unambiguously identified. One major metabolite was detected by liquid chromatography/mass spectrometry-radioactivity in urine from monkeys treated with the aryl piperazine oral hypoglycemic agent 9-[(1S,2R)-2-fluoro-1-methylpropyl]-2-methoxy-6-(1-piperazinyl) purine hydrochloride (1). The mass spectrum of this metabolite indicated that it was both monooxygenated and glucuronidated on the piperazine ring. Possible structures included the N-or O-glucuronic acid conjugates of a carbinolamine, hydroxylamine, or N-oxide. Treatment with ␤-glucuronidase gave a monooxygenated derivative of the parent compound. H NMR analysis of either the glucuronic acid conjugateor the monooxygenated product provided insufficient evidence to unambiguously determine their structures. Incubation of 1 with pig liver microsomes resulted in formation of the same monooxygenated derivative derived from ␤-glucuronidase treatment of the glucuronide metabolite. This in vitro system was used to generate sufficient material for analysis by 13 C NMR, and the metabolite was identified as a hydroxylamine derivative 2. Incubation of the hydroxylamine with monkey liver microsomes and uridine diphospho-5-glucuronic acid gave the same glucuronic acid conjugate as that observed in monkey urine. 13

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“…After stopping nortriptyline the estimated half-life of nortriptyline was 24 h (in the expected range), suggesting that the interaction was caused by increased bioavailability rather than decreased clearance compared to nifedipine argue for an interaction between nortriptyline and diltiazem. by N-hydroxylation [6] and by N-demethylation [5]. The major metabolic pathway of diltiazem in man is demethylation, catalysed by the CYP3A subfamily [3].…”

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confidence: 99%